4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-13-(triethylsilyloxy)-11-taxene

Base Information

• Chemical Name: 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-13-(triethylsilyloxy)-11-taxene
• CAS No.: 1396601-24-3
• Molecular Formula: C₃₇H₅₄O₁₀Si
• Molecular Weight: 686.915

Synonyms:4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-13-(triethylsilyloxy)-11-taxene

Chemical Property of 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-13-(triethylsilyloxy)-11-taxene

Chemical Property:

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Technology Process of 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-13-(triethylsilyloxy)-11-taxene

There total 7 articles about 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-13-(triethylsilyloxy)-11-taxene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.6%

4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,7β-dihydroxy-9-oxo-10β-methoxy-13α-triethylsilyloxy-11-taxene (1433749-82-6) + methyl iodide (74-88-4) → 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-13-(triethylsilyloxy)-11-taxene (1396601-24-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at -5 - 0 ℃;

Reference yield: 70.0%

triethylsilyl chloride (994-30-9) + 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene (183133-94-0) → 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-13-(triethylsilyloxy)-11-taxene (1396601-24-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 120h;

DOI:10.1016/j.bioorg.2021.105578

Reference yield:

13β-triethylsilyl-10-deacetylbaccatin III + methyl iodide (74-88-4) → 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-13-(triethylsilyloxy)-11-taxene (1396601-24-3)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

upstream raw materials:

4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,7β-dihydroxy-9-oxo-10β-methoxy-13α-triethylsilyloxy-11-taxene

methyl iodide

4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,10β-dihydroxy-9-oxo-7β,13α-di(triethylsilyloxy)-11-taxene

4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-9-oxo-10β-methoxy-7β,13α-di(triethylsilyloxy)-11-taxene

Downstream raw materials:

4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene

carbazitaxel

(αR, βS)-α-hydroxy-β-[[(1,1-dimethylethoxy)carbonyl]amino]benzene-propanoic acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,1112,12a,12b-dodecahydro-11-hydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester isopropanol solvate

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